Hydrogen Peroxide → 3'-Deoxy-3'-(3-hydroxypropyl)-5'-O-tert-butyldiphenylsilylthymidine

HRID 2288269Notes

Reaction equation

HRID 2288269 reaction equation
[CH2:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:5]1)[CH:2]=[CH2:3].O.C([O-])(O)=[O:39].[Na+].OO>C1COCC1>[OH:39][CH2:3][CH2:2][CH2:1][C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:7][C@@H:6]([N:28]2[CH:36]=[C:34]([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:5]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 516892Sodium BicarbonateHCID 154508083'-Deoxy-3'-allyl-5'-O-tert-butyldiphenylsilylthymidine

Product 1

HCID 228782693'-Deoxy-3'-(3-hydroxypropyl)-5'-O-tert-butyldiphenylsilylthymidineYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 37 (0.74 g, 2 mmol) was treated with BH3Me2S (0.388 g, 5.12 mmol) in THF (10 ml). The reaction mixture was quenched with MeOH (0.7 mL). H2O (3 mL) and NaHCO3 (1.11 g, 13.3 mmol) were added to the reaction mixture followed by H2O2 (30%, 1.91 mL, 16.92 mmol). After work-up, the residue was purified by silica gel chromatography. The product was crystallized from ether/hexane to furnish 0.41 g of the product as white needles. mp 150-151° C.

Workup

  1. customThe reaction mixture was quenched with MeOH (0.7 mL)
  2. customAfter work-up, the residue was purified by silica gel chromatography
  3. customThe product was crystallized from ether/hexane

Sources & evidence

ORD record
ord-13d679f8f6504165ac4cd46e1e7cea42
Source dataset
uspto-grants-2000_07
Patent number
US06087482

Reaction notes

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